Fast-curing epoxy systems

Patent metadata

Field	Value
Publication number	US-11370876-B2
Application number	US-201916408794-A
Country	US
Kind code	B2
Filing date	May 10, 2019
Priority date	May 17, 2018
Publication date	Jun 28, 2022
Grant date	Jun 28, 2022

Abstract

The present invention relates to a low-alkylphenol composition comprising a) at least one epoxy resin, b) at least one amine having at least two secondary amino groups that are both part of an organic ring system, and c) at least one salt of a strong Brønsted acid with a counterion selected from metal ions, metal-containing ions, phosphonium ions and ammonium ions, to processes for production thereof and to the use thereof.

First claim

The invention claimed is:

1. A low-alkyl phenol composition comprising:
a) an epoxy resin,
b) a cyclic amine having at least two secondary cyclic amino groups belonging to the same cycle of the cyclic amine,
c) a salt of a Brønsted acid,
d) a diamine or polyamine, which is not a cyclic amine having at least two secondary cyclic amino groups belonging to the same cycle of the cyclic amine, and
e) optional auxiliaries and/or additives;
wherein a) is present in an amount of from 30 to 95 wt %, based on the total weight of the composition;
wherein b) is present in an amount of from 1 to 50 wt %, based on the total weight of the composition, and is selected from the group consisting of 1H-octahydroimidazo[4,5-c]pyridine, 1,4,8-triazaspiro[4.5]decane, 1,4-diazaspiro[4.5]decane, pyrazolidine, 2,2-dimethylimidazolidine, 1,4,7-triazacyclononane, hexahydropyridazine, tetradecahydrophenazine, decahydroquinoxaline, octahydro-1H-cyclopentapyrazine, piperazine, 2-methylpiperazine, 2,2-dimethylpiperazine, 2,3-dimethylpiperazine, 2-ethylpiperazine, 2,5-dimethylpiperazine, 2,6-dimethylpiperazine, 2,3,5,6-tetramethylpiperazine, 2,3,5-trimethylpiperazine, 2-(2-piperidinyl)piperazine, homopiperazine, 2-methylhomopiperazine, and 6-methyl-1,4-diazepane;
wherein c) is present in an amount of from 0.001 to 5 wt %, based on the total weight of the composition, the Brønsted acid of the salt has a pKa of from 2 to −9, and the counterion of the salt is selected from a metal ion, a metal-containing ion, a phosphonium ion, and a NH 4 ion;
wherein d) is present in an amount such that b) accounts for at least 70 wt % of the combined weight of b) and d) in the composition;
wherein e) are optionally present in an amount of up to 48 wt %, based on the total weight of the composition; and
wherein alkylphenols are present in an amount of not more than 10% by weight, based on the total weight of the composition.

2. The low-alkylphenol composition according to claim 1 , wherein
the epoxy resin a) is selected from the group consisting of bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, 4,4′-methylenebis[N,N-bis(2,3-epoxypropyl)aniline], hexanediol diglycidyl ether, butanediol diglycidyl ether, trimethylolpropane triglycidyl ether, propane-1,2,3-triol triglycidyl ether, pentaerythritol tetraglycidyl ether and diglycidyl hexahydrophthalate; and wherein alkylphenols are present in an amount of not more than 9% by weight, based on the total weight of the composition.

3. The low-alkylphenol composition according to claim 2 , wherein
alkylphenols are present in an amount of not more than 7% by weight, based on the total weight of the composition.

4. The low-alkylphenol composition according to claim 3 , wherein
alkylphenols are present in an amount of not more than 5% by weight, based on the total weight of the composition.

5. The low-alkylphenol composition according to claim 1 , wherein
alkylphenols are present in an amount of not more than 8% by weight, based on the total weight of the composition.

6. The low-alkylphenol composition according to claim 1 , wherein
the counterion of the salt of a Brønsted acid c) is selected from an alkaline earth metal ion, lithium ion, zirconium ion, phosphonium ion, and a NH 4 ion, and wherein alkylphenols are not present in the composition.

7. The low-alkylphenol composition according to claim 1 , wherein the Brønsted acid of the salt of a Brønsted acid c) is selected from oxalic acid, p-toluenesulfonic acid, trifluoroacetic acid, tetrafluoroboric acid, nitric acid, sulfuric acid, hydrochloric acid, and hydrobromic acid.

8. The low-alkylphenol composition according to claim 1 , wherein
the optional auxiliaries and/or additives e) are present in an amount of up to 48 wt %, based on the total weight of the composition.

9. The low-alkylphenol composition according to claim 8 , wherein
the diamine or the polyamine d) is selected from the group consisting of
aliphatic diamines or polyamines,
oxyalkylenepolyamines,
cycloaliphatic diamines or polyamines,
diamines or polyamines having a cyclic amino group and at least one acyclic primary or secondary amino group,
araliphatic diamines or polyamines,
aromatic diamines or polyamines,
adduct hardeners of diamines or polyamines,
polyamidoamine hardeners,
Mannich base hardeners of diamines or polyamines, and
Mannich bases of diamines or polyamines.

10. A process for producing a low-alkyl phenol composition according to claim 1 ,
wherein the a), b), c), d) and optionally e) are mixed with one another.

11. A composite comprising the low-alkylphenol composition according to claim 1 .

12. A casting resin comprising the low-alkylphenol composition according to claim 1 .

13. A coating composition comprising the composition according to claim 1 .

14. An adhesive comprising the low-alkylphenol composition according to claim 1 .

Assignees

• Evonik Operations Gmbh

Inventors

• Spyrou Emmanouil
• Fuchsmann Dirk
• Kohlstruk Britta
• Sandkühler Annette

Classifications

• C08G59/5073

  having two nitrogen atoms in the ring · CPC title

• C08G59/5053 Primary

  containing only nitrogen as a heteroatom · CPC title

• C08G59/22

  Di-epoxy compounds · CPC title

• C08G59/506 Primary

  having one nitrogen atom in the ring · CPC title

• C08G59/682

  Alcoholates · CPC title